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Solid‐phase synthesis of a dendritic peptide related to a retinoblastoma protein fragment utilizing a combined boc‐ and fmoc‐chemistry approach
Author(s) -
Cavallaro Vittoria,
Thompson Philip,
Hearn Milton
Publication year - 2001
Publication title -
journal of peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 66
eISSN - 1099-1387
pISSN - 1075-2617
DOI - 10.1002/psc.314
Subject(s) - chemistry , peptide synthesis , solid phase synthesis , peptide , retinoblastoma , combinatorial chemistry , sequence (biology) , chemical synthesis , molecule , fragment (logic) , biochemistry , organic chemistry , in vitro , computer science , gene , programming language
Dendritic peptides, often presented as multiple antigen peptides (MAPs), are widely used in immunological‐based fields of research, although their synthesis can be extremely challenging. In this paper, a tetrameric dendritic MAP‐like presentation of the retinoblastoma protein [649‐654] sequence (4RB 649‐654 ) has been prepared using solid‐phase peptide synthesis (SPPS) methods. During the synthesis of this dendritic molecule, numerous modifications to the synthetic protocols were examined. These modifications included the introduction of a combination Boc‐ and Fmoc‐chemistry approach and also the use of 1,8‐diazabicyclo[5.4.0]‐undec‐7‐ene as a Fmoc‐deprotection agent. The use in combination of Boc‐ and Fmoc‐based synthetic strategies resulted in the production of the desired peptide molecule, 4RB 649‐654 , in high purity and acceptable yields following purification by reversed phase HPLC. Copyright © 2001 European Peptide Society and John Wiley & Sons, Ltd.